Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesizing method of indole and indolizine ketone compounds

A technology of indolizinone and synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as no literature report, and achieve the effects of rich variety, concise and efficient synthesis method, and wide adaptability of substrates

Inactive Publication Date: 2019-05-31
HUAIHAI INST OF TECH
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many types of indolezine derivatives, and the synthesis of indolezine derivatives has been reported in the literature, but for the use of β-indoleamine and β-butynoic acid as raw materials, acetylacetonate metal complex As a catalyst, the method for one-step synthesis of indolo indoxazinone compounds has not been reported in the literature

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesizing method of indole and indolizine ketone compounds
  • Synthesizing method of indole and indolizine ketone compounds
  • Synthesizing method of indole and indolizine ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The reaction formula is:

[0019]

[0020] Add 10mmol (5-methyl-1H-indol-3-yl)methanamine, 12mmol 3-pentynoic acid and 10mL ionic liquid [BMIm]Br into the reaction flask, stir until dissolved, then add 0.5mmol catalyst Cu( acac) 2 , continue to stir for about 0.5h, then raise the temperature to 70°C, stir for another 6h, and detect the reaction progress by thin-layer chromatography. Add 20mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, use 95% ethanol as solvent Recrystallization was carried out to obtain the target product with a yield of 92%.

Embodiment 2

[0022] The reaction formula is:

[0023]

[0024] Add 10mmol (5-chloro-1H-indol-3-yl)methanamine, 12mmol 3-butynoic acid and 10mL ionic liquid [HMIm]Cl into the reaction flask, stir until dissolved, then add 0.6mmol catalyst Vo(acac ) 2 , continue to stir for about 0.5h, then raise the temperature to 80°C, stir and react for 8h, and detect the reaction process by thin-layer chromatography. Add 20 mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, and use 95% ethanol as the solvent for After recrystallization, the target product was obtained with a yield of 86%.

Embodiment 3

[0026] The reaction formula is:

[0027]

[0028] Add 10mmol (5-methoxy-1H-indol-3-yl)methanamine, 12mmol 4-(p-tolyl)-3-butynoic acid and 10mL ionic liquid [BMMIm]Br into the reaction flask, stir to dissolve Then add 0.8mmol catalyst Ni(acac) 2 , continue to stir for about 0.5h, then raise the temperature to 75°C, stir for another 7h, and detect the reaction process by thin-layer chromatography. Add 20mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, use 95% ethanol as solvent Recrystallization was carried out to obtain the target product with a yield of 80%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesizing method of indole and indolizine ketone compounds. Chemical equation of the synthesizing method is shown in the description, wherein R1 and R2 represent groups onaromatic rings and nitrogen atoms of 3-indole methylamine compounds respectively, R3 represents groups on triple bonds of 3-tetrolic acid compounds, a catalyst is acetylacetone metal complex, and thegeneral formula of the catalyst is M(acac)2; ionic liquid is [BMIm]X, [PMIm]X, [HMIm]X, [BMMIm]X, [BMMIm]BF4 and [EMIm]BF4. The synthesizing method of the indole and indolizine ketone compounds is novel, easy and efficient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing indoloindoxazinone compounds. Background technique [0002] Nitrogen-containing heterocyclic compounds are important organic molecules, which widely exist in medicine, pesticide and material molecules. Indole is an important nitrogen-containing aromatic heterocyclic compound with potential biological activity. It has irreplaceable importance in the synthesis of pharmaceuticals, materials and bioactive molecules. It has become the core structural unit of many drug molecules; indolezine is also a It is an important nitrogen-containing heterocyclic compound, but it is sensitive to light and is easily oxidized in the air to cause ring damage, which limits its application in organic synthesis to a certain extent. However, in recent years, with the development of medicinal chemistry Development, indoxazine derivatives have shown very goo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D471/04
Inventor 王启发胡浩强程青芳王丹苏欣宇曹一鸣
Owner HUAIHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com